In a casual Italian restaurant just outside of Las Vegas, veteran sports handicapper Bryan Leonard considers a stromboli and looks less than thrilled. Glancing up at a flat-screen TV before checking the menu, he says, “It’s desperation time. I’m 0 and 2; he’s 2 and 0.” Then, maybe feeling a need to tease out the pain a little more, Leonard adds, “His early pick was Houston and they kicked a field goal, with three minutes left, to win it.”

The he that Leonard refers to is a successful, professional sports bettor by the name of Mike Greene. Each man has put up $5,000 to compete in Cantor Gaming’s Football Showdown 2012, held at the M. Resort, situated south of the Las Vegas Strip. Combining elements of a heads-up poker tournament with that of traditional sports betting, the event this year was a magnet for the sharp and the savvy. The tournament begins with eight brackets; in each of those brackets, two gamblers go up against one another. Whoever picks the most winners continues playing against an increasingly slender field.

Already having bitten the dust are well-known sports bettor Steve Fezzik and handicapper Adam Meyer. The contest began with a field of 16, Cantor Gaming kicked in $10,000 to provide positive equity for all contenders, and Leonard and Greene have made it to the final two. Winner gets $67,500; runner-up receives $22,500. It’s not exactly the set of steak knives that Alec Baldwin’s character promises to the second-best salesman during his famously brutal monologue in Glengarry Glen Ross, but the money will be nice and the bragging rights will be just as sweet.

For Leonard, who’s already been runner-up in three major handicapping contests, the pressure to win this one is acute. Plus, his handicapping business, footballwinners.com, through which he sells picks to gamblers, will surely get a boost of credibility if he aces the Cantor event. Unfortunately for him, with only five games remaining in this final bracket, Leonard needs a minor miracle to come out ahead. Though he just looks resigned on the outside, on the inside, I assume, he’s a bag of nerves. “I still get stressed over these things,” he acknowledges. “I’ve broken stuff out of frustration. I used to have a partner who punched holes in the walls. That’s not good to do in front of your employees.”

In terms of the game we are watching, Pittsburgh Steelers vs. Dallas Cowboys, Leonard has taken the under, betting that the score will total less than 44. It is not going well for him at all. When a Steelers player dips into the end zone, ball first, Leonard looks sick. He smiles tightly and says, “It’s like walking through a bad neighborhood and knowing you will either be shot or stabbed. I just got shot.”

The game goes into overtime and the Cowboys win, 27–24. The score totals 51, and Leonard goes to a disheartening 0 and 3. If there is a silver lining, it’s that his opponent, Mike Greene, lost his bet as well, now standing at 2 and 1. Surmising his situation while we wait for the check, Leonard says, “I have to go 4 and 0 and Mike needs to go 2 and 2.”It’s not the sort of statement that he’s hoping for me to offer commentary on.

Sports-betting tournaments are not only for Vegas’s most seasoned, highest rolling handicappers and are not relegated to the football season. March Madness, that great splash of NCAA Finals basketball games, comes with its own tournament. Known as Last Man Standing, put on by Station Casinos and as sensible a gamble as you’re likely to find, it requires that you keep selecting winners throughout the run of basketball games. You pick one game per day, going against the spread; mess up once and you’re out of the running. But whoever makes it to the end will receive a fabulous windfall. The entry fee is only $25—additionally, you get five entries for the price of four—and the payoff last year was $53,300 (the casino takes no commission; that sum accounts for the free entries that contestants received when they purchased four).

For casual gamblers, Last Man Standing might be as good as it gets in Vegas sports betting. “The average gambler loves to risk a little to win a lot,” says RJ Bell, who runs the sports-betting newssite pregame.com. “And if you look at it in terms of economic theory, it makes a lot of sense. Plus you get to have daily action for a small amount of money. Usually, with that sort of arrangement, say, a typical parlay bet, you need to pay a high commission to the casino. But Station looks at it as a way of drumming up business, so all the entry fees go back into the prize pool, and you get a shot at winning decent money.”

The Last Man Standing tournament has been going strong for nine years, and there is at least one good way to capitalize on its structure. Because the contest point spreads come out between 7 a.m. and 8 a.m. each morning—and remain unchanged throughout the day—you can use the casino’s continually changing line for individual bets to gauge where the smart money is going. “There may be more information and you may get a good deal by waiting,” says Chuck Esposito, director of race and sports book operations at Sunset Station. But there’s a potential downside. “The point spread may not move at all and you begin to limit the number of games you have to choose from. Then what happens if you like Team A and the line moves against you?”

Of course you can take the other side of the bet. Or, even better, since you probably will have multiple entries, you can space your bets through the day, using certain entries for early bets, when there is less information available (in terms of how the teams might play as well as line movements) and use others for later in the day (when you have fewer games to choose from but stronger information).

As the days of March Madness pass, and you keep winning, the value of your entry fee goes up while the number of opponents goes down. This is the point where you can find some leverage. If your buy-in was worth $20.46 when there were, say, 2,604 entries and $53,300 in the pot, by the time there are 50 contenders left, each ticket is worth $1,066. If somebody is willing to buy one-fifth of your potential winnings for $213, you lock in a profit, whether or not you win the tournament.

During football season, Station offers a series of different low buy-in tournaments, including a Last Man Standing. The one where you can’t possibly lose, though, is the season-long Great Giveaway. It offers a variety of wagering formats, and, as long as you enter every week and always lose, you get back your entry fees in free slot-play when the season is over. “That,” says Bryan Leonard, “is a no-brainer for anyone in town. I have friends who don’t follow sports at all, and they get into the Station contest because it gives them something to root for and won’t cost them anything.”

Regardless of what kind of sports-betting tournament you enter—the largest and the longest running is the Las Vegas Hilton’s SuperContest, which goes through the NFL season and attracted 745 contestants in 2012, each of whom put up $1,500 to buy in—there is one golden rule that should be followed: Never take a bad number. “Guys come in with their best bets, and they stick to it regardless of the point spread,” says Leonard. “I don’t do it that way. I handicap numbers, not teams.” His point is that in betting tournaments, you rarely get the best number. If it’s moved into a worse spot, he explains, you need a good reason to bet it under that condition. Otherwise, you’re putting yourself at a disadvantage.

Steve Fezzik has a sensible, simple solution: “Go across the street and make the bet that you want to make. Then find a more favorable opportunity for the tournament.”

While everyone suggests doing all of the standard research on games and teams and trying to figure out how your opponent tends to bet—RJ Bell calls that “the meta game”—Fezzik takes it a step further. He uses a popular and reliable tout, whom he calls Mr. J., as a barometer. The idea is that he tracks the suggested bets Mr. J. puts out to his thousands of customers and sees how those customers react. “If a big-name handicapper likes a side and the line does not move at all, I take the other side,” says Fezzik. “When you have all these subscribers paying for information and they do not take it, that should tell you something about the public’s opinion.”

RJ Bell suggests approaching tournament betting with a contrarian point of view. As he explains, your average bettor tends to put money on favorites and marquee teams. This means that the Dukes of the world get loads of play during March Madness. “If you bet around the public teams, you’ll see a lot of people getting eliminated while you have a shot at staying in the tournament,” says Bell. “If, for example, you think Duke is the best team of the day, and they have a 20-percent chance of losing but your next-best team is off the radar and has a 22-percent chance of losing, you’re better off picking the less likely team. If you win and Duke loses, then a big chunk of the field is gone. If you are in a contest, you are not only competing against the spread, but you’re also competing against the other participants. That is very different from straight-ahead sports betting.”

Additionally, tournaments can be used as tools to augment your standard sports betting. Cantor finalist Mike Greene explains that he created a no-lose situation for himself. “I hedged against the contest each week,” he says, pointing out that he would see the sides that his opponent took and then mirror those wagers independent of the tournament. “You’re getting the picks of professional handicappers, and if they win in the contest, at least you win your bets. If you don’t win on the wagers, you most likely move up in the contest [because the other guy lost].”

And it doesn’t hurt to have a sounding board of trusted friends who can offer feedback on your opinions. Bryan Leonard meets with a group of fellow handicappers every Tuesday. They sit around and hash out the coming week’s games. Additionally, he had a partner, a very sharp professional gambler who’d rather not be named, with whom he worked on making picks. The only wrinkle arose when the partner was in Italy, carving up a casino there, and Internet trouble caused communication problems right before bets were to be placed.

Greene had no such advantage. “I felt like it was me against a lot of sharp minds,” he says. However, Greene does acknowledge that lone-wolf anonymity gave him a bit of an advantage in at least one area: “I wasn’t worried about what anyone thought of my picks. A lot of guys [with local reputations] concern themselves with what people will think of their selections. They don’t want to pick favorites or make square bets. I didn’t care what anyone thought. If they want to think I’m a square, fine. Let them. If I think seven favorites will win, I will take them. I’m not worried about what people think of my picks.”

He’s not kidding. On the last card of the event, playing in the final, five favorites took up seven of his picks.

Anybody who thought that Mike Greene had a lock just because he had an advantage going into the final round of games was sadly mistaken. “I was very ahead at the beginning,” Greene acknowledges, weeks after my meal with Bryan Leaonard. “But Bryan won a bunch of games by New Year’s Day. We were at the point where if he won two more games, I would have lost the contest.”

How was he feeling in the days leading up to New Year’s? “There was a lot of work and stress and angst.”

Then, on January 5, when the Mississippi Rebels played against the Pittsburgh Panthers in the NCAA Compass Bowl, Greene was rooting for Ole Miss, which he had picked. Leonard had selected Pittsburgh at plus-three. When Mississippi won 38–17, Greene knew he’d be receiving a windfall. However, the celebration was muted and the cash prize went straight into his bankroll. “I had a nice dinner that evening,” says Greene. “But it was more relief than celebration. I went into the final with a big lead and felt the contest slowly slipping away.”

And for a gambler who makes a living out of beating sports, there was something more than money at play. It’s part of what drove Greene, normally a low-profile guy, to enter such a public event in the first place. “I did it out of pride and money,” he acknowledges, pointing out that going up against gamblers is a dimension beyond simply going up against a sports book.

“First it was positive equity, since we all put up $5,000 and the casino kicked in $10,000. Then, even though it was anxiety provoking, the contest gave me a chance to go head-to-head with quality people. It was very competitive and, coming in as a bit of an outsider, very gratifying to beat these guys.”Michael Kaplan is a Cigar Aficionado contributing editor.